Waldoboro Vacation Rentals from CA $127: Short-Term Rentals for 2026

Q: What are some of the best vacation home rentals that Waldoboro has to offer?

Oceanview Bungalow Style Home in Owls Head : This vacation home rental outside Waldoboro is located by the ocean and has a balcony, a terrace, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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Our top choices for Waldoboro vacation rentals

1. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Waldoboro

CA $256 total

includes taxes & fees

Oct 17 - Oct 18

A two-story white building with a symmetrical facade, large windows with shutters, and a central entrance with a door and columns.

2. The Entire Waldoboro Inn

Waldoboro

CA $1,542 total

includes taxes & fees

Oct 12 - Oct 13

A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

3. Come Spring Farm Airstream , Lake & farm animals

Union

Thomas W.

CA $362 total

includes taxes & fees

Oct 18 - Oct 19

A campfire surrounded by rocks and two wooden Adirondack chairs.

4. Glamping at Maine Water Buffalo Farm

Appleton

Gary

CA $232 total

includes taxes & fees

Oct 8 - Oct 9

A cabin with a wooden exterior, a glass door, and a sign indicating it is a camp.

5. Tiny A-Frame Romantic Getaway

Wiscasset

lisa s.

CA $575 total

includes taxes & fees

Oct 21 - Oct 22

6. Trade Winds on the Bay

Rockland

Allene

CA $127 total

includes taxes & fees

Oct 20 - Oct 21

A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

7. Simplicity-Just what you need! STR24-20

Rockland

sarah

CA $216 total

includes taxes & fees

Oct 20 - Oct 21

A wooden deck with a glass door leading to a room.

8. Tiny Cottage Near Everything 10

Edgecomb

Gene

CA $313 total

includes taxes & fees

Nov 2 - Nov 3

A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

9. 2 Bedroom Close to Town Home

Thomaston

Brianna M.

CA $370 total

includes taxes & fees

Nov 1 - Nov 2

A bedroom with a bed, a bedside table, and a window with curtains.

10. Peaceful Intown Studio ~ Walk to Shops & Dining

Newcastle

Brian

CA $256 total

includes taxes & fees

Oct 14 - Oct 15

A wooden deck with Adirondack chairs and a grill.

11. Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston

Alexis H.

CA $356 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

12. Cheerful Cottage Close to Everything 12

Edgecomb

Tom C.

CA $317 total

includes taxes & fees

Oct 27 - Oct 28

A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

13. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Union

Sabrina D.

CA $360 total

includes taxes & fees

Oct 12 - Oct 13

A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

14. Peaceful, Centrally Located Home with Seasonal River Views

Thomaston

Pastor Heidi G.

CA $423 total

includes taxes & fees

Nov 2 - Nov 3

A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

15. Cheerful Cottage with Loft 9

Edgecomb

Daniel B.

CA $334 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

16. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Thomaston

Stephen H.

CA $529 total

includes taxes & fees

Oct 20 - Oct 21

17. Romantic Coastal Escape near Harbor

Rockport

"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...

Christopher H.

CA $375 total

includes taxes & fees

Oct 25 - Oct 26

A room with a large window offering a view of a snowy landscape and a body of water.

18. Comfortable, Close to Town Home, with Oceanview.

Owls Head

Rich W.

CA $528 total

includes taxes & fees

Oct 25 - Oct 26

Two Adirondack chairs facing a body of water with a bridge in the background.

19. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Edgecomb

Ann M.

CA $441 total

includes taxes & fees

Oct 26 - Oct 27

A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

20. A Spacious Vacation Cottage in Sheepscot Harbour

Edgecomb

Julie D.

CA $441 total

includes taxes & fees

Oct 25 - Oct 26

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Top Waldoboro Hotel Reviews

Harborline Hotel

10/10 Excellent

"Excellent parking, nice location. Reasonable value and well-appointed room. Breakfast was pretty basic but satisfactory."

Boothbay Harbor Inn

8/10 Good

"Nice hotel, room was clean, bed was Ok, need more pillows. Bathroom was well lit and stocked with products, shower pressure was not good. Parking could be a challenge at times. The walking bridge to the other side of the bay was very close and a short walk to lots of shops and restaurants. there is no elevator just steps. It was not easy bringing our heavy suitcases up to the second floor. If I went back booth bay harbor I would probably stay again on the ground floor."

Trade Winds on the Bay

10/10 Excellent

"Decent hotel in a great location, very central to downtown Rockland and the boardwalk is a 4 minute walk away. Fairly clean, but could use some slightly better blinds for the window (got the room with no outside window, but still one to the hallway) AC works, but is a bit loud, still slept great though. Would stay again and recommend it."

Find out more about Waldoboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Waldoboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Waldoboro?

Yes, there are vacation rentals in Waldoboro close to Morse's Sauerkraut, or you can go with a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the gardens in Waldoboro. Make sure you have time to check out the local tours and bars during your trip.

What are some of the best vacation home rentals that Waldoboro has to offer?

Oceanview Bungalow Style Home in Owls Head: This vacation home rental outside Waldoboro is located by the ocean and has a balcony, a terrace, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Waldoboro?

With 22 Expedia vacation rentals, you're sure to find just the right place for your Waldoboro stay.

What’s there to see and do in Waldoboro?

Pemaquid Pond and Duckpuddle Pond are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Morse's Sauerkraut. In the larger area, you’ll find Fawcett's Antique Toy and Art Museum and St. George River.

What’s a vacation rental in Waldoboro like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Waldoboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Waldoboro vacation rentals

1. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

2. The Entire Waldoboro Inn

3. Come Spring Farm Airstream , Lake & farm animals

4. Glamping at Maine Water Buffalo Farm

5. Tiny A-Frame Romantic Getaway

6. Trade Winds on the Bay

7. Simplicity-Just what you need! STR24-20

8. Tiny Cottage Near Everything 10

9. 2 Bedroom Close to Town Home

10. Peaceful Intown Studio ~ Walk to Shops & Dining

11. Bright 2-Bedroom Apartment Near Downtown Thomaston

12. Cheerful Cottage Close to Everything 12

13. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

14. Peaceful, Centrally Located Home with Seasonal River Views

15. Cheerful Cottage with Loft 9

16. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

17. Romantic Coastal Escape near Harbor

18. Comfortable, Close to Town Home, with Oceanview.

19. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

20. A Spacious Vacation Cottage in Sheepscot Harbour

Find vacation rentals that suit your style

Top Waldoboro Hotel Reviews

Harborline Hotel

Camden Riverhouse Hotel

Boothbay Harbor Inn

Rockland Harbor Hotel

The Country Inn at Camden Rockport

Trade Winds on the Bay

Cedar Crest Inn

Camp DeForest

Flagship Inn and Suites

Find out more about Waldoboro

Frequently asked questions

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